US20250068073A1 - Photosensitive resin composition - Google Patents

Photosensitive resin composition Download PDF

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Publication number
US20250068073A1
US20250068073A1 US18/724,013 US202218724013A US2025068073A1 US 20250068073 A1 US20250068073 A1 US 20250068073A1 US 202218724013 A US202218724013 A US 202218724013A US 2025068073 A1 US2025068073 A1 US 2025068073A1
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Prior art keywords
resin composition
photosensitive resin
mass
styrene
liquid
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US18/724,013
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English (en)
Inventor
Yoshikazu Ueno
Yosuke Uehara
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Kuraray Co Ltd
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Kuraray Co Ltd
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Assigned to KURARAY CO., LTD. reassignment KURARAY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: UEHARA, YOSUKE, UENO, YOSHIKAZU
Publication of US20250068073A1 publication Critical patent/US20250068073A1/en
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M1/00Inking and printing with a printer's forme
    • B41M1/02Letterpress printing, e.g. book printing
    • B41M1/04Flexographic printing
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/06Butadiene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F287/00Macromolecular compounds obtained by polymerising monomers on to block polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0384Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the main chain of the photopolymer
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41PINDEXING SCHEME RELATING TO PRINTING, LINING MACHINES, TYPEWRITERS, AND TO STAMPS
    • B41P2200/00Printing processes
    • B41P2200/10Relief printing
    • B41P2200/12Flexographic printing
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/22Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having three or more carbon-to-carbon double bonds

Definitions

  • a known photoinitiator such as an aromatic ketone or a benzoin ether
  • examples thereof include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropanone, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropanone, 4-(2-hydroxyethoxy)-phenyl (2-hydroxy-2-propyl) ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholynopropanone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin phenyl ether, benzyl dimethyl ketal, benzophenone, be
  • One of the photoinitiator (D) may be used alone or two or more thereof may be used in combination.
  • benzyl dimethyl ketal, diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, and phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide are preferred, and benzyl dimethyl ketal is more preferred.
  • photoinitiator (D) commercial products, such as trade names: “Irgacure 184”, “Irgacure 127”, “Irgacure 149”, “Irgacure 261”, “Irgacure 369”, “Irgacure 500”, “Irgacure 651”, “Irgacure 754”, “Irgacure 784”, “Irgacure 819”, “Irgacure 907”, “Irgacure 1116”, “Irgacure 1173”, “Irgacure 1664”, “Irgacure 1700”, “Irgacure 1800”, “Irgacure 1850”, “Irgacure 2959”, “Irgacure 4043”, “Darocure (registered trademark: hereinafter omitted) 1173”, and “Darocure MBF” (all manufactured by BASF), are suitably used.
  • the content of the photoinitiator (D) based on the total amount of the photosensitive resin composition is preferably 0.1 to 10% by mass, more preferably 0.5 to 5% by mass.
  • the content of the photoinitiator (D) is 0.1% by mass or more, the formability of fine points and characters on the printing plate can be enhanced, and when the content is 10% by mass or less, the transmittance of active light, such as ultraviolet light, can be enhanced.
  • the photosensitive resin composition of the present invention may contain, besides the thermoplastic elastomer (A), the liquid farnesene rubber (B), the ethylenically unsaturated compound (C), and the photoinitiator (D), other components, such as an antioxidant, a plasticizer, a filler, a colorant, a thermal polymerization inhibitor, an ultraviolet light absorber, a halation inhibitor, and a photostabilizer.
  • the contents of the other components are not particularly limited as long as the effect of the present invention is not impaired, and, based on the total amount of the photosensitive resin composition, are preferably 0.1 to 50% by mass, more preferably 0.5 to 40% by mass, further preferably 0.5 to 30% by mass.
  • the method for producing the photosensitive resin composition of the present invention is not particularly limited, and any method that can uniformly mix the thermoplastic elastomer (A), the liquid farnesene rubber (B), the ethylenically unsaturated compound (C), the photoinitiator (D), and the aforementioned other compounds can be preferably employed.
  • a method in which melt-mixing is performed using a single screw extruder, a twin screw extruder, a kneader, a bunbury mixer, or the like is preferably employed.
  • the kneading temperature is preferably 100 to 200° C., more preferably 120 to 180° C.
  • the photosensitive resin composition after kneading can be molded into a sheet having a desired thickness by calender roll, press, extrusion, or the like.
  • the photosensitive resin composition of the present invention can be used as a layer constituting a laminated body.
  • the photosensitive resin composition of the present invention preferably shows a tendency to have a low tackiness before curing as compared with a photosensitive resin composition that comprises an alternative to the liquid farnesene rubber (B) which can be an object to be compared.
  • a photosensitive resin composition that comprises an alternative to the liquid farnesene rubber (B) which can be an object to be compared.
  • the photosensitive resin composition of the present invention preferably shows a tendency to give a low tackiness after curing as compared with a photosensitive resin composition that comprises an alternative to the liquid farnesene rubber (B) which can be an object to be compared.
  • a flexographic printing plate having a photosensitive layer composed of the photosensitive resin composition has a suppressed stickiness, which suppresses attachment of dust and tear of an object to be printed in printing, thus being superior in the printing performance.
  • the photosensitive resin composition according to one embodiment has a tackiness before curing at 25° C. of preferably 9.5 N or less, more preferably 7.5 N or less, further preferably 6.5 N or less, furthermore preferably 6.0 N or less, and particularly preferably 5.5 N or less.
  • thermoplastic elastomer (A) contains a styrene-butadiene-styrene block copolymer
  • thermoplastic elastomer (A) contains a styrene-butadiene-styrene block copolymer
  • the liquid farnesene rubber (B) contains a monomer unit (a) and a monomer unit (b).
  • the lower limit of the tackiness before curing at 25° C. is not particularly limited, and, for example, is 0.1 N or more. When the tackiness before curing at 25° C. is 9.5 N or less, the effect as described above is more significantly exhibited.
  • the photosensitive resin composition according to said one embodiment has a tackiness after curding at 25° C. of preferably 3.0 N or less, more preferably 2.5 N or less, further preferably 2.0 N or less.
  • the lower limit of the tackiness after curding at 25° C. is not particularly limited, and, for example, is 0.1 N or more. When the tackiness after curding at 25° C. is 3.0 N or less, the effect as described above is more significantly exhibited.
  • the photosensitive resin composition according to another embodiment has a tackiness before curing at 25° C. of preferably less than 14.3 N, more preferably 13.5 N or less, further preferably 13.3 N or less.
  • the thermoplastic elastomer (A) contains a styrene-isoprene-styrene block copolymer
  • the thermoplastic elastomer (A) contains a styrene-isoprene-styrene block copolymer
  • the liquid farnesene rubber (B) has a content of the monomer unit (a) of 100% by mass.
  • the lower limit of the tackiness before curing at 25° C. is not particularly limited, and, for example, is 0.1 N or more. When the tackiness before curing at 25° C. is less than 14.3 N, the effect as described above is more significantly exhibited.
  • the photosensitive resin composition according to said another embodiment has a tackiness after curding at 25° C. of preferably less than 6.3 N, more preferably 6.2 N or less, further preferably 6.1 N or less.
  • the lower limit of the tackiness after curding at 25° C. is not particularly limited, and, for example, is 0.1 N or more. When the tackiness after curding at 25° C. is less than 6.3 N, the effect as described above is more significantly exhibited.
  • the cured product of the photosensitive resin composition of the present invention preferably shows a tendency to have a low rate of extraction of components into a solvent, such as toluene.
  • a flexographic printing plate having a photosensitive layer composed of the photosensitive resin composition is suppressed in the temporal change in properties and thus, is superior in the stability of the printing performance.
  • a cured product of the photosensitive resin composition of the present invention more preferably shows such a tendency to have a low tackiness before and after curing as described above while showing a tendency to have a low rate of extraction of components into a solvent, such as toluene.
  • the rate of extraction of the liquid farnesene rubber (B) of a cured product of the photosensitive resin composition can be measured by a method described in the section of Examples.
  • a cured product of the photosensitive resin composition according to said one embodiment has a rate of extraction of the liquid farnesene rubber (B) after immersion in toluene at 25° C. for 48 hours of preferably 15.0% by mass or less, more preferably 10.0% by mass or less, further preferably 8.0% by mass or less.
  • a rate of extraction of the liquid farnesene rubber (B) after immersion in toluene at 25° C. for 48 hours of preferably 15.0% by mass or less, more preferably 10.0% by mass or less, further preferably 8.0% by mass or less.
  • a cured product of the photosensitive resin composition according to said another embodiment has a rate of extraction of the liquid farnesene rubber (B) after immersion in toluene at 25° C. for 48 hours of preferably 20.0% by mass or less, more preferably 19.0% by mass or less, further preferably 18.0% by mass or less.
  • a rate of extraction of the liquid farnesene rubber (B) after immersion in toluene at 25° C. for 48 hours of preferably 20.0% by mass or less, more preferably 19.0% by mass or less, further preferably 18.0% by mass or less.
  • a cured product of the photosensitive resin composition according to said another embodiment tends to be able to exhibit the aforementioned effect to show a tendency to have a low tackiness before and after curing while showing a tendency to have a low rate of extraction.
  • a cured product of the photosensitive resin composition of the present invention preferably shows a tendency to have a low glass transition temperature (Tg) as compared with a cured product of a photosensitive resin composition that comprises an alternative to the liquid farnesene rubber (B) which can be an object to be compared.
  • Tg low glass transition temperature
  • B liquid farnesene rubber
  • Tg of a cured product of the photosensitive resin composition can be measured by a method described in the section of Examples.
  • a cured product of the photosensitive resin composition according to said one embodiment has a glass transition temperature (Tg) of preferably ⁇ 80° C. or lower, more preferably ⁇ 84° C. or lower, further preferably ⁇ 86° C. or lower.
  • Tg glass transition temperature
  • the cured product of the photosensitive resin composition according to said another embodiment has a glass transition temperature (Tg) of preferably ⁇ 57° C. or lower, more preferably ⁇ 59° C. or lower, further preferably ⁇ 61° C. or lower.
  • Tg glass transition temperature
  • the flexographic printing plate of the present invention has a photosensitive layer composed of the photosensitive resin composition described above.
  • a sheet of the photosensitive resin composition is placed on a support, and the support and the sheet of the photosensitive resin composition is brough into a close contact by roll lamination, followed by hot press, thereby obtaining a constituent body for a flexographic printing plate in which a photosensitive layer is formed on the support.
  • the thickness of the photosensitive layer is generally 0.5 to 7 mm, preferably 0.5 to 3.5 mm.
  • the thickness of the printing plate is generally 0.5 to 7.0 mm, preferably 0.5 to 3.5 mm.
  • the thickness of the printing plate can be changed depending on the object to be printed.
  • the amounts of the components blended in the photosensitive resin composition may be changed, or with reference to said another embodiment, the thermoplastic elastomer (A) in the photosensitive resin composition may contain a styrene-isoprene-styrene block copolymer.
  • the hardness of the printing plate is generally a type A hardness of 28 to 74, preferably 30 to 65.
  • the hardness of the printing plate can be measured with a type A durometer according to JIS K6253-3:2012.
  • the harness of the printing plate can be changed depending on the object to be printed.
  • the hardness of the printing plate is to be increased according to the object to be printed, for example, when the type A hardness is required to be 60 or more according to the thickness of the printing plate being 3.0 mm or less, the amounts of components blended in the photosensitive resin composition may be changed, or with reference to said another embodiment, the thermoplastic elastomer (A) in the photosensitive resin composition may contain a styrene-isoprene-styrene block copolymer. Said another embodiment is particularly suitable when the printing plate has a small thickness and a high hardness.
  • a general method for forming a flexographic printing plate from the constituent body for the flexographic printing plate first, the entire surface thereof is subjected to ultraviolet light exposure through the support (back exposure) to provide a thin uniform cured layer on the interface of the photosensitive layer with the support, and then, thorough a negative film that covers the top of the photosensitive layer, the surface of the photosensitive layer is subjected to image exposure (relief exposure) to ultraviolet light. Then an unexposed part of the photosensitive layer is washed out with a developer, or is thermally melted and then removed by absorption with an absorbing layer, followed by post treatment exposure, thus producing a flexographic printing plate.
  • exposure to ultraviolet light of a wavelength in the range of 200 to 300 nm, followed by exposure to ultraviolet light of a wavelength in the range of 310 to 400 nm may be performed.
  • the exposure on the negative film side (relief exposure) and the exposure on the support side (back exposure) may be performed in either order or may be performed at the same time.
  • Examples of the light source for the exposure include a high-pressure mercury lamp, an ultraviolet light fluorescent lamp, a carbon ark lamp, a xenon lamp, or a diode lamp.
  • Examples of a developing solvent used for developing the unexposed part include esters, such as heptyl acetate and 3-methoxybutyl acetate, hydrocarbons, such as a petroleum fraction, toluene, and decalin, and a solvent in which an alcohol, such as propanol, butanol, or pentanol, is mixed with a chlorine-based organic solvent, such as tetrachloroethylene.
  • esters such as heptyl acetate and 3-methoxybutyl acetate
  • hydrocarbons such as a petroleum fraction, toluene, and decalin
  • a solvent in which an alcohol, such as propanol, butanol, or pentanol is mixed with a chlorine-based organic solvent, such as tetrachloroethylene.
  • the washing out of the unexposed part with the developing solvent is performed by a jet from a nozzle or by brushing with a brush.
  • a method in which the surface is irradiated with light of a wavelength of 300 nm or shorter is generally used.
  • light having a wavelength longer than 300 nm may be used together.
  • ⁇ -Farnesene (purity: 97.6% by mass, manufactured by Amyris Biotechnologies) was purified by purification with a 3 ⁇ -molecular sieve, followed by distillation under a nitrogen atmosphere to remove hydrocarbon impurities, such as Zingiberene, Bisabolenes, farnesene epoxide, farnesol isomers, E,E-farnesol, squalene, ergosterol, and several types of dimers of farnesene.
  • hydrocarbon impurities such as Zingiberene, Bisabolenes, farnesene epoxide, farnesol isomers, E,E-farnesol, squalene, ergosterol, and several types of dimers of farnesene.
  • liquid polyfarnesene butadiene copolymers (B-1) to (B-3), the liquid polyfarnesene (B-4), and the liquid polybutadienes (b-1) to (b-3) obtained in Production Examples 1 to 7 were evaluated for properties according to methods shown below. The results are shown in Table 1.
  • Mw, Mn, and Mw/Mn of the liquid polymers were determined by molecular weights based on standard polystyrenes by GPC (gel permeation chromatography).
  • the measurement apparatuses and conditions are as follows.
  • the vinyl content was determined according to the following method.
  • part A (spectrum derived from vinyl structure of farnesene unit)
  • part B synthetic spectrum of spectrum derived from vinyl structure of farnesene unit and spectrum derived from 1,13-bond
  • part C (spectrum derived from vinyl structure of butadiene unit) Part of 5.22 to 5.65 ppm: part D (synthetic spectrum of spectrum derived from vinyl structure of butadiene unit and spectrum derived from 1,4-bond)
  • thermogram was measured with a differential scanning calorimeter (DSC) under a condition of a temperature increase rate of 10° C./min, and the peak top value of DDSC was taken as the glass transition temperature (Tg).
  • DSC differential scanning calorimeter
  • the melt viscosity at 38° C. of each liquid polymer was measured with a Brookfield viscometer (manufactured by BROOKFIELD ENGINEERING LABS. INC.).
  • the resulting photosensitive resin composition was made into a form in which both surfaces were covered with a polyester film as a cover sheet having a thickness of 100 ⁇ m, and was molded with a press machine having a temperature set to 140° C. to produce a sheet (hereinafter also referred to as uncured sheet) having a thickness of 2 mm.
  • the resulting uncured sheet was irradiated with ultraviolet light using a UV irradiation machine (manufactured by Heraeus: mercury xenon lamp) under conditions of an illuminance of 500 mJ/cm 2 and an integrated quantity of light of 8000 mJ/cm 2 , thereby producing a sheet (hereinafter also referred to as cured sheet) having a thickness after curing of 2 mm.
  • a UV irradiation machine manufactured by Heraeus: mercury xenon lamp
  • Each of the uncured sheets and cured sheets was cut into a size of 2 cm ⁇ 10 cm.
  • the cover sheet of the uncured sheet or cured sheet was peeled off, and using PICMA Tack Tester (manufactured by TOYO SEIKI SEISAKU-SHO, LTD.) as a measurement apparatus, the tackiness (stickiness) was measured by a method in which a stainless steel plate and a surface of the uncured sheet or cured sheet were brought into contact for 4 seconds at a rate of 10 mm/min, and then the uncured sheet or cured sheet was peeled from the surface of the stainless steel plate at a rate of 10 mm/min in a vertical direction.
  • the cured sheet obtained in each of Examples and Comparative Examples was punched into a diameter of 32 mm, and the cover sheet was peeled off, and the cured sheet was immersed in 100 ml of toluene at 25° C. for 48 hours, and then, the rate of extraction of the liquid polymer extracted from the cured sheet was calculated based on the weight change.
  • thermogram was measured with a differential scanning calorimeter (DSC) under a condition of a temperature increase rate of 10° C./min, and the peak top value of DDSC was taken as the glass transition temperature (Tg). Note that the measurement apparatuses and conditions are the same as those in the measurement of the glass transition temperature of liquid polymers.
  • the photosensitive resin compositions of Examples 1-1 to 1-5 give a low tackiness before and after curing, a low rate of extraction of a liquid polymer after curing, and a low glass transition temperature of a sheet after curing.
  • the resulting photosensitive resin composition was made into a form in which both surfaces were covered with a polyester film as a cover sheet having a thickness of 100 ⁇ m, and was molded with a press machine having a temperature set to 140° C. to produce a sheet (uncured sheet) having a thickness of 2 mm.
  • the resulting uncured sheet was irradiated with ultraviolet light using a UV irradiation machine (manufactured by Heraeus; mercury xenon lamp) under conditions of an illuminance of 500 mJ/cm 2 and an integrated quantity of light of 8000 mJ/cm 2 , thereby producing a sheet (cured sheet) having a thickness after curing of 2 mm.
  • a UV irradiation machine manufactured by Heraeus; mercury xenon lamp
  • Example 2-1 Example 2-2
  • the photosensitive resin compositions of Examples 2-1 to 2-2 can provide photosensitive resin compositions that give a low tackiness before and after curing while maintaining a low rate of extraction after curing. It is also seen in Table 3 that the photosensitive resin compositions of Example 2-1 to 2-2 also give a low glass transition temperature of a sheet after curing.
  • the photosensitive resin composition of the present invention has a low tackiness before curing, even when a negative film is directly placed on a photosensitive layer composed of the photosensitive resin composition, the negative film can be easily peeled after image exposure to allow the negative film to be reused.
  • the photosensitive resin composition of the present invention gives a low tackiness after curing, a printing plate having a photosensitive layer composed of the photosensitive resin composition has a suppressed stickiness, which suppresses attachment of dust and tear of an object to be printed in printing, and thus being superior in printing performance.
  • the photosensitive resin composition of the present invention has a trend to give a low rate of extraction of a liquid polymer after curing, a printing plate having a photosensitive layer composed of the photosensitive resin composition is suppressed in temporal changes in properties, and thus being superior in stability of the printing performance. Accordingly, the photosensitive resin composition of the present embodiment is suitably used for a flexographic printing plate.

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  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
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